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WO2010091193A3 - Triptolide c-ring derivatives as anticancer agents and immune modulators - Google Patents

Triptolide c-ring derivatives as anticancer agents and immune modulators Download PDF

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Publication number
WO2010091193A3
WO2010091193A3 PCT/US2010/023220 US2010023220W WO2010091193A3 WO 2010091193 A3 WO2010091193 A3 WO 2010091193A3 US 2010023220 W US2010023220 W US 2010023220W WO 2010091193 A3 WO2010091193 A3 WO 2010091193A3
Authority
WO
WIPO (PCT)
Prior art keywords
triptolide
anticancer agents
immune modulators
ring derivatives
ring
Prior art date
Application number
PCT/US2010/023220
Other languages
French (fr)
Other versions
WO2010091193A2 (en
Inventor
John H. Musser
Original Assignee
Pharmagenesis, Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Pharmagenesis, Inc. filed Critical Pharmagenesis, Inc.
Priority to EP10739131.0A priority Critical patent/EP2393818A4/en
Priority to US13/147,587 priority patent/US8268882B2/en
Priority to CA2750844A priority patent/CA2750844A1/en
Priority to JP2011549263A priority patent/JP5653939B2/en
Priority to CN201080006751.4A priority patent/CN102307881B/en
Priority to AU2010210594A priority patent/AU2010210594B2/en
Publication of WO2010091193A2 publication Critical patent/WO2010091193A2/en
Publication of WO2010091193A3 publication Critical patent/WO2010091193A3/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J73/00—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms
    • C07J73/001—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom
    • C07J73/003—Steroids in which the cyclopenta[a]hydrophenanthrene skeleton has been modified by substitution of one or two carbon atoms by hetero atoms by one hetero atom by oxygen as hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
    • C07D493/16—Peri-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/12—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains three hetero rings
    • C07D493/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/22—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains four or more hetero rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Animal Behavior & Ethology (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Immunology (AREA)
  • Transplantation (AREA)
  • Biomedical Technology (AREA)
  • Neurology (AREA)
  • Neurosurgery (AREA)
  • Pain & Pain Management (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

Disclosed are compounds based on C- and D-ring modifications of triptolide and hydroxylated triptolide, for use in therapy, such as antiproliferative, anticancer, and immunosuppressive therapy.
PCT/US2010/023220 2009-02-05 2010-02-04 Triptolide c-ring derivatives as anticancer agents and immune modulators WO2010091193A2 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
EP10739131.0A EP2393818A4 (en) 2009-02-05 2010-02-04 Triptolide c-ring derivatives as anticancer agents and immune modulators
US13/147,587 US8268882B2 (en) 2009-02-05 2010-02-04 Triptolide C-ring derivatives as anticancer agents and immune modulators
CA2750844A CA2750844A1 (en) 2009-02-05 2010-02-04 Triptolide c-ring derivatives as anticancer agents and immune modulators
JP2011549263A JP5653939B2 (en) 2009-02-05 2010-02-04 Triptolide C-ring derivatives as anticancer agents and immunomodulators
CN201080006751.4A CN102307881B (en) 2009-02-05 2010-02-04 Tripolide C-ring derivatives as anticancer agents and immune modulators
AU2010210594A AU2010210594B2 (en) 2009-02-05 2010-02-04 Triptolide C-ring derivatives as anticancer agents and immune modulators

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US15020709P 2009-02-05 2009-02-05
US61/150,207 2009-02-05

Publications (2)

Publication Number Publication Date
WO2010091193A2 WO2010091193A2 (en) 2010-08-12
WO2010091193A3 true WO2010091193A3 (en) 2011-02-03

Family

ID=42542652

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2010/023220 WO2010091193A2 (en) 2009-02-05 2010-02-04 Triptolide c-ring derivatives as anticancer agents and immune modulators

Country Status (7)

Country Link
US (1) US8268882B2 (en)
EP (1) EP2393818A4 (en)
JP (1) JP5653939B2 (en)
CN (2) CN102307881B (en)
AU (1) AU2010210594B2 (en)
CA (1) CA2750844A1 (en)
WO (1) WO2010091193A2 (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TWI480040B (en) * 2012-06-11 2015-04-11 Univ Kaohsiung Medical Use of triptolide for manufacturing a medicament for treating a disease related to survival motor neuron protein expression
WO2014031979A1 (en) 2012-08-23 2014-02-27 Dyer, Cheryl, A. Reducing the reproductive capacity of mammals

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003101951A2 (en) * 2002-05-31 2003-12-11 Pharmagenesis, Inc. Triptolide derivatives for modulation of apoptosis and immunosuppression
WO2004058246A1 (en) * 2002-12-17 2004-07-15 Pharmagenesis, Inc. Triptolide derivatives as immunomodulator and anticancer agents
WO2004075853A2 (en) * 2003-02-25 2004-09-10 Pharmagenesis, Inc. Halogenated triptolide derivatives as immunomodulators and anticancer agents
WO2005084365A2 (en) * 2004-03-02 2005-09-15 Pharmagenesis, Inc. Triptolide lactone ring derivatives as immunomodulators and anticancer agents

Family Cites Families (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4005108A (en) 1973-04-03 1977-01-25 Research Corporation Novel anti-leukemic diterpenoid triepoxides
CN1027371C (en) * 1989-09-08 1995-01-11 中国医学科学院皮肤病研究所 Method for synthesizing diterpene lactone compound
AU7570191A (en) 1990-03-14 1991-10-10 Board Of Regents, The University Of Texas System Tripterygium wilfordii hook f extracts and components thereof for immunosuppression
US5663335A (en) * 1996-03-01 1997-09-02 Pharmagenesis, Inc. Immunosuppressive compounds and methods
US6004999A (en) * 1997-05-23 1999-12-21 Hoechst Marion Roussel, Inc. Triptolide derivatives useful in the treatment of autoimmune diseases
ATE222910T1 (en) * 1997-05-23 2002-09-15 Aventis Pharma Inc TRIPTOLIDE DERIVATIVES USEFUL FOR TREATING AUTOIMMUNE DISEASES
ATE334969T1 (en) * 1998-09-02 2006-08-15 Pharmagenesis Inc TRIPTOLIDE PRODRUGS WITH HIGH WATER SOLUBILITY
JP2001081030A (en) * 1999-07-13 2001-03-27 Mitsuhiro Hatta Side-effect protective agent in immunosuppresant
WO2002017931A1 (en) 2000-09-01 2002-03-07 Xiaomin Wang Use of tripterygium wilfordii hook.f's extracts for preparation of medicaments for preventing and treating nervous system disorde rs
US6620843B2 (en) 2001-01-19 2003-09-16 Pharmagenesis Anticancer treatment using triptolide prodrugs
CA2448795A1 (en) * 2001-03-15 2002-09-26 Pharmagenesis, Inc. Amino acid derivatives of triptolide compounds as immune modulators and anticancer agent
JP2004168713A (en) * 2002-11-20 2004-06-17 St Marianna Univ School Of Medicine Apoptosis inducer
CN100408583C (en) * 2003-02-25 2008-08-06 美国泛华医药公司 Halogenated triptolide derivatives as immunomodulators and anticancer agents
WO2005020887A2 (en) 2003-06-27 2005-03-10 Pharmagenesis, Inc. Method for treatment of severe acute respiratory syndrome
WO2005062913A2 (en) * 2003-12-24 2005-07-14 Pharmagenesis, Inc. Triplide 5,6-derivatives as immunomodulators and anticancer agents
CN100374443C (en) * 2004-03-29 2008-03-12 北京键凯科技有限公司 Hydrophilic polymer-thunder good vine extract binding substance and its medicinal composition
WO2009023201A1 (en) * 2007-08-16 2009-02-19 Myelorx Llc Rigid derivatives of triptolide as anticancer, immune suppressant, anti-fibrosis, and cns protectant agents

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2003101951A2 (en) * 2002-05-31 2003-12-11 Pharmagenesis, Inc. Triptolide derivatives for modulation of apoptosis and immunosuppression
WO2004058246A1 (en) * 2002-12-17 2004-07-15 Pharmagenesis, Inc. Triptolide derivatives as immunomodulator and anticancer agents
WO2004075853A2 (en) * 2003-02-25 2004-09-10 Pharmagenesis, Inc. Halogenated triptolide derivatives as immunomodulators and anticancer agents
WO2005084365A2 (en) * 2004-03-02 2005-09-15 Pharmagenesis, Inc. Triptolide lactone ring derivatives as immunomodulators and anticancer agents

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
PHOEBE A. PHILLIPS ET AL: "Triptolide Induces Pancreatic Cancer Cell Death via Inhibition of Heat Shock Protein 70", CANCER RES., vol. 67, no. 19, 2007, pages 9407 - 9416, XP009135086 *
QIUYAN LIU ET AL: "Immunosuppressant triptolide inhibits dendritic cell-mediated chemoattraction of neutrophils and T cells through inhibiting Stat3 phosphorylation and NF-KB activation", BIOCHEM. BIOPHYS. RES. COMMUN., vol. 345, no. 3, 2006, pages 1122 - 1130, XP024925203 *

Also Published As

Publication number Publication date
CN102307881B (en) 2014-12-24
US20110288166A1 (en) 2011-11-24
EP2393818A2 (en) 2011-12-14
CA2750844A1 (en) 2010-08-12
JP5653939B2 (en) 2015-01-14
US8268882B2 (en) 2012-09-18
WO2010091193A2 (en) 2010-08-12
EP2393818A4 (en) 2013-09-04
CN102307881A (en) 2012-01-04
AU2010210594B2 (en) 2015-02-12
AU2010210594A1 (en) 2011-08-18
JP2012516899A (en) 2012-07-26
CN104387406A (en) 2015-03-04

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